IN THE SUPREME COURT OF IOWA

No. 06–1812

Filed June 26, 2009

STATE OF IOWA,

Appellee,

vs.

NATHAN JOHN CARROLL,

Appellant.

On review from the Iowa Court of Appeals.

Appeal from the Iowa District Court for Scott County, Bobbi M. 

Alpers (guilty plea) and John A. Nahra (sentencing), Judges. 

Nathan Carroll seeks further review of a court of appeals decision 

affirming his conviction following a guilty plea. Carroll asserts his 

conviction based on the guilty plea was the result of ineffective 

assistance of counsel and should be set aside. DECISION OF THE 

COURT OF APPEALS VACATED; DISTRICT COURT JUDGMENT 

AFFIRMED.

Kent A. Simmons, Davenport, for appellant.

Thomas J. Miller, Attorney General, Kevin Cmelik, Assistant 

Attorney General, William E. Davis, County Attorney, and Amy DeVine, 

Assistant County Attorney, for appellee.
2

HECHT, Justice.

We granted further review of a decision of the court of appeals 

affirming Nathan Carroll’s conviction and sentence for possession with 

intent to deliver marijuana. Carroll contends the conviction based upon 

his guilty plea should be set aside because the plea was a product of 

ineffective assistance of counsel. In particular, he contends his plea was 

neither voluntary nor intelligent because his attorney was ineffective in 

failing to file a motion to suppress evidence obtained as a result of a 

warrantless search, and in failing to give proper advice in advance of the 

plea. We conclude the record is inadequate to decide Carroll’s 

ineffective-assistance-of-counsel claim. Accordingly, we affirm his 

conviction and sentence, and we preserve the claim for possible 

postconviction relief proceedings. 

I. Factual and Procedural Background.

In February 2006 police officers responded to a report of a party 

with underage consumption of alcohol in LeClaire, Iowa. Upon arrival at 

the address to which they were dispatched without a search warrant, the 

officers found a dwelling, and behind it, a barn from which the sounds of 

the party were emanating. After following an unidentified male and 

female through a door into the barn, the officers observed several 

juveniles drinking alcohol. A preliminary breath test disclosed Carroll 

had consumed alcohol. He was cited, along with several other juveniles, 

for possession of alcohol under the legal age. During a search of the 

barn, the officers located a marijuana “blunt,” a baggie filled with 

marijuana, and a brick of marijuana. The officers arrested Cory Wulf, 

the host of the party, for illegal possession of the marijuana. 

The next morning Carroll appeared at the LeClaire Police 

Department. Carroll spoke with an officer who prepared a written report 
3

stating Carroll claimed ownership of the drugs found the previous 

evening in the Wulf barn. Carroll was subsequently charged with 

possession of marijuana with intent to deliver in violation of Iowa Code 

section 124.401(1)(d) (2005) and possession of the drugs without a drug 

tax stamp in violation of Iowa Code sections 453B.1(3)(b), 453B.7(1), 

453B.12, and 703.1. 

Carroll and the State reached a plea agreement. Under the 

agreement, Carroll agreed to plead guilty to the drug possession with 

intent to deliver charge, and the State agreed to dismiss the drug tax 

stamp charge and recommend against incarceration.1

The district court rejected Carroll’s request for a deferred judgment 

at the subsequent sentencing hearing, noting Carroll continued to use 

marijuana during the months following the incident which was the 

subject of the guilty plea in this case.

 Carroll 

subsequently pled guilty to possession with intent to deliver, and the 

drug tax stamp charge was dismissed consistent with the plea 

agreement. 

2 Doubting Carroll’s appreciation of 

the seriousness of his conduct, the court sentenced Carroll to a term of 

imprisonment not to exceed five years, suspended the sentence, and 

ordered a term of probation of two years.3

Carroll appealed his conviction asserting his trial counsel provided 

ineffective assistance by failing to (1) file a motion to suppress evidence 

seized in an illegal search of the Wulf premises, (2) challenge the 

sufficiency of the evidence to support a conviction on the drug 

 1The State agreed to make the sentencing recommendation “recognizing the 

Court may grant a deferred judgment.”

2Carroll candidly admitted his continued use of marijuana during an interview 

with the presentence investigator.

3The presentence investigation report recommended probation in this case.
4

possession charges, and (3) adequately prepare Carroll for the sentencing 

proceeding, and present the case supporting imposition of a deferred 

judgment at the sentencing hearing. Carroll also challenged his 

sentence, contending the district court abused its discretion by basing its 

decision solely upon Carroll’s continued use of marijuana after 

February 24, 2006. We transferred the case to the court of appeals for 

decision, and that court affirmed the conviction and sentence.4

Carroll sought further review of the decision of the court of 

appeals. We granted Carroll’s request for review to consider whether 

ineffective assistance of counsel rendered Carroll’s guilty plea 

uninformed and involuntary.

II. Discussion.

A. Applicable Legal Principles. A claimant alleging ineffective 

assistance of counsel must prove (1) counsel failed to perform an 

essential duty and (2) prejudice resulted. State v. Risdal, 404 N.W.2d 

130, 131–32 (Iowa 1987). To establish prejudice, a claimant must 

demonstrate “ ‘there is a reasonable probability that, but for the 

counsel’s unprofessional errors, the result of the proceeding would have 

been different.’ ” State v. Reynolds, 746 N.W.2d 837, 845 (Iowa 2008) 

(quoting State v. Shanahan, 712 N.W.2d 121, 136 (Iowa 2006)); see also

Strickland v. Washington, 466 U.S. 688, 694, 104 S. Ct. 2052, 2068, 80 

L. Ed. 2d 674, 698 (1984). In the context of a guilty plea, an applicant 

for postconviction relief must prove “ ‘a reasonable probability that, but 

for counsel’s alleged errors, he [or she] would not have pled guilty and 

would have insisted on going to trial.’ ” State v. Straw, 709 N.W.2d 128, 

 4The court of appeals concluded Carroll’s guilty plea waived any claims of 

ineffective assistance of counsel as to the failure to file a motion to suppress and the 

failure to challenge the sufficiency of the evidence, concluding those claims were “not a 

circumstance that bears on the knowing and voluntary nature of a plea.”
5

136 (Iowa 2006) (quoting Hill v. Lockhart, 474 U.S. 52, 59, 106 S. Ct. 

366, 370, 88 L. Ed. 2d 203, 210 (1985)). The probability of a different 

result must be “ ‘sufficient to undermine confidence in the outcome.’ ” 

Anfinson v. State, 758 N.W.2d 496, 499 (Iowa 2008) (quoting Reynolds, 

746 N.W.2d at 845). We will address on direct appeal claims of 

ineffective assistance of counsel only if we determine the development of 

an additional factual record would not be helpful and these elements can 

be decided as a matter of law. See State v. Tesch, 704 N.W.2d 440, 450 

(Iowa 2005). 

It is well established that a defendant’s guilty plea waives all 

defenses and objections which are not intrinsic to the plea. State v. 

Antenucci, 608 N.W.2d 19, 19 (Iowa 2000). The State contends the 

claims that the warrantless search of Wulf’s barn was illegal and that 

evidence obtained as a consequence of that search should have been 

suppressed were waived by Carroll’s guilty plea because they are not 

matters intrinsic to the plea. Carroll controverts the State’s waiver 

argument, positing his claims on appeal were not waived because they 

are based on the proposition that his defense counsel was ineffective in 

failing to (1) comprehend that the warrantless search of the barn was 

illegal, (2) file a motion to suppress all evidence derived from the search, 

and (3) properly advise Carroll as to whether he should enter a guilty 

plea in light of the circumstances surrounding the warrantless search of 

Wulf’s barn. These claimed failures of counsel, Carroll asserts, were 

intrinsic to the plea because they caused him to improvidently plead 

guilty to a charge that the State could not have proven had counsel 

performed effectively. Our resolution of this issue is aided by a review of 

the case law addressing the extent to which a guilty plea waives 
6

defendant’s defenses and objections and eliminates them as a ground for 

relief on direct appeal and in postconviction proceedings. 

A defendant’s guilty plea is not necessarily rendered involuntary 

merely because it follows his defense counsel’s mistaken assessment of 

the admissibility of the State’s evidence. Parker v. North Carolina, 397 

U.S. 790, 796–97, 90 S. Ct. 1458, 1462, 25 L. Ed. 2d 785, 791–92

(1970). This proposition is based upon the fact that criminal cases in 

general, and guilty pleas in particular, are characterized by considerable 

uncertainty:

[T]he decision to plead guilty before the evidence is in 

frequently involves the making of difficult judgments. All the 

pertinent facts normally cannot be known unless witnesses 

are examined and cross-examined in court. Even then the 

truth will often be in dispute. In the face of unavoidable 

uncertainty, the defendant and his counsel must make their 

best judgment as to the weight of the State’s case. Counsel 

must predict how the facts, as he understands them, would 

be viewed by a court. If proved, would those facts convince a

judge or jury of the defendant’s guilt? On those facts would 

evidence seized without a warrant be admissible? Would the 

trier of fact on those facts find a confession voluntary and 

admissible? Questions like these cannot be answered with 

certitude; yet a decision to plead guilty must necessarily rest 

upon counsel’s answers, uncertain as they may be. Waiving 

trial entails the inherent risk that the good-faith evaluations 

of a reasonably competent attorney will turn out to be 

mistaken either as to the facts or as to what a court’s 

judgment might be on given facts.

McMann v. Richardson, 397 U.S. 759, 769–70, 90 S. Ct. 1441, 1448, 25 

L. Ed. 2d 763, 772–73 (1970) (citing Brady v. United States, 397 U.S. 

742, 756–57, 90 S. Ct. 1463, 1473–74, 25 L. Ed. 2d 747, 760–61 (1970)). 

Thus, “a defendant’s plea of guilty based on reasonably competent advice 

is an intelligent plea not open to attack on the ground that counsel may 

have misjudged the admissibility of the defendant’s confession.” Id. at 

770, 90 S. Ct. at 1448, 25 L. Ed. 2d at 773; see also State v. Freilinger, 

557 N.W.2d 92, 93 (Iowa 1996) (stating guilty plea “ ‘waives all 
7

irregularities except that the information or indictment charges no 

offense and the right to challenge the plea itself’ ” (quoting State v. Door, 

184 N.W.2d 673, 674 (Iowa 1971))); State v. Culbert, 188 N.W.2d 325, 

326 (Iowa 1971) (same). 

A defendant can, however, challenge the validity of his guilty plea 

by proving the advice he received from counsel in connection with the 

plea was not within the range of competence demanded of attorneys in 

criminal cases. Tollett v. Henderson, 411 U.S. 258, 265–67, 93 S. Ct. 

1602, 1607–08, 36 L. Ed. 2d 235, 242–43 (1973); Zacek v. Brewer, 241 

N.W.2d 41, 48–49 (Iowa 1976) (noting that although a defendant may 

not, after entry of a guilty plea, raise independent claims relating to the 

deprivation of constitutional rights that occurred prior to the plea, he 

may attack the voluntary and intelligent character of the plea by showing 

the advice received from counsel was not within the range of competence 

demanded of attorneys in criminal cases). 

“Counsel’s failure to evaluate properly facts giving rise to a 

constitutional claim, or his failure to properly inform himself 

of facts that would have shown the existence of a 

constitutional claim, might in particular fact situations meet 

this standard of proof.” 

Zacek, 241 N.W.2d at 49 (quoting Tollet, 411 U.S. at 266–67, 93 S. Ct. at 

1608, 36 L. Ed. 2d at 243). Although we announced in Zacek our 

adherence to the rule that a counsel’s breach of duty calling into 

question whether a defendant’s guilty plea was intelligently and 

voluntarily entered may support a challenge to the plea, our application 

of the rule in subsequent cases has created some confusion. 

B. Application of Legal Principles. In Speed v. State, 616 

N.W.2d 158 (Iowa 2000), an applicant for postconviction relief contended 

his guilty plea should be set aside because his attorney provided 
8

ineffective assistance in failing to seek suppression of his confession. 

616 N.W.2d at 159. In affirming the district court’s decision denying 

Speed’s claim for postconviction relief, our per curiam opinion cryptically 

noted the general rule that “claims arising from the denial of a motion to 

suppress or from counsel’s failure to investigate or file a motion to 

suppress do not survive the entry of a guilty plea.”5

Carroll contends his counsel provided ineffective assistance in 

failing to file a meritorious motion to suppress evidence derived from an 

illegal warrantless search. For the sake of discussion only, let us 

assume two hypothetical cases. In the first case (1) the search of Wulf’s 

barn was in fact illegal; (2) all evidence obtained by the State as a 

consequence of the search would have been suppressed if a motion 

 Id. We now revisit 

the general rule and find it lacking in its application to cases in which 

defendants on direct appeal or applicants for postconviction relief assert 

they would not have pled guilty but for the ineffective assistance of their 

counsel. 

 5In support of this proposition we cited State v. Culbert, 188 N.W.2d 325 (Iowa 

1971), State v. Freilinger, 557 N.W.2d 92 (Iowa 1996), and State v. Sharp, 572 N.W.2d 

917 (Iowa 1997). Two of these three cases did not present the question of whether 

claimed ineffective assistance of counsel led to unintelligent or involuntary guilty pleas, 

and they are therefore not instructive on the issue now before us. Culbert presented on 

direct appeal the question whether a guilty plea waived a claim that the defendant’s 

confession was involuntary, and the appellant notably did not contend his plea and 

conviction should be set aside as a consequence of ineffective assistance of counsel. 

188 N.W.2d at 325–26. Similarly, in Freilinger, the appellant brought a direct appeal 

following his entry of a guilty plea, but he made no claim that the plea and resulting 

conviction should be set aside because his attorney’s ineffectiveness caused the plea to 

be unintelligently or involuntarily entered. 557 N.W.2d at 93–94. Of the three cases, 

only Sharp presented claims that counsel’s ineffectiveness rendered a guilty plea 

unintelligent and involuntary. 572 N.W.2d at 918–19, superseded by statute on other 

grounds as recognized in Wyciskalla v. Iowa Dist. Ct., 588 N.W.2d 403, 406–07 (Iowa 

1998). In Sharp, we concluded without further analysis that counsel’s failure to 

investigate the circumstances surrounding the defendant’s arrest and failure to seek 

suppression of a blood test “did not survive the plea of guilty.” Id. Other unspecified 

claims of ineffectiveness raised by Sharp were “matters that [bore upon] the question of 

whether [his] guilty plea was intelligently and voluntarily entered,” and our decision 

preserved them for possible postconviction proceedings. Id. at 919.
9

requesting such relief had been filed; (3) a reasonably competent attorney 

would have known or discovered the factual and legal basis for the 

meritorious suppression motion, informed Carroll of the likely outcome of 

the meritorious motion, requested authority from Carroll to file it, and 

advised Carroll not to plead guilty to a felony; (4) Carroll’s attorney failed 

to do these things a reasonably competent attorney would have done and 

advised Carroll to plead guilty; and (5) Carroll, believing his attorney had 

performed effectively, expecting to be convicted at trial of all charges, and 

relying on his attorney’s advice, pled guilty. In the second hypothetical 

case, we shall assume the circumstances are exactly the same except the 

attorney advises Carroll to go to trial, the evidence that should have been 

suppressed is admitted, and Carroll is convicted. Our decision in Speed 

fails to explain why the law should provide Carroll a remedy under the 

circumstances assumed in the second hypothetical, but not in the first. 

It is not sensible to hold that the defendant in the first case should bear 

the negative consequences of counsel’s ineffective assistance because he 

pled guilty, but the defendant in the second case should get a second 

chance for justice because he chose a trial. We conclude there is no 

principled explanation for such disparity for in both cases the defendant 

did not receive effective counsel guaranteed by the Sixth Amendment and 

suffered prejudice. We therefore disavow our decision in Speed insofar 

as it suggests claims of ineffective assistance arising from counsel’s 

failure to investigate or file a meritorious motion to suppress cannot, as a 

matter of law, survive the entry of a guilty plea.

Faithful application of the rule announced in Zacek precludes 

Speed’s broad conclusion that “counsel’s failure to investigate or file a 

motion to suppress do not survive the entry of a guilty plea.” Id. We 

conclude there are no such categories of breach of duty resulting in 
10

prejudice that cannot, as a matter of law, survive a guilty plea. Only 

through a case-by-case analysis will a court be able to determine 

whether counsel in a particular case breached a duty in advance of a 

guilty plea, and whether any such breach rendered the defendant’s plea 

unintelligent or involuntary. As in any other case in which relief is 

requested as a consequence of alleged ineffective assistance of counsel, 

the party claiming his counsel provided ineffective assistance in advance 

of the entry of a guilty plea must prove counsel breached a duty and 

prejudice resulted. Risdal, 404 N.W.2d at 131–32; see Strickland, 466 

U.S. at 694, 104 S. Ct. at 2068, 80 L. Ed. 2d at 698. The burden to 

prove prejudice in this context will require the party seeking relief to 

prove a reasonable probability of a different outcome had the breach not 

occurred; i.e., that but for counsel’s breach of duty, the party seeking 

relief would not have pled guilty and would have elected instead to stand 

trial. Straw, 709 N.W.2d at 136; see Strickland, 466 U.S. at 694, 104 

S. Ct. at 2068, 80 L. Ed. 2d at 698.

C. Was Carroll’s Claim of Involuntariness Properly Raised? In 

his initial appeal brief, Carroll contended the police officers’ warrantless 

entry into and search of the barn were illegal, and asserted his counsel 

was therefore ineffective in failing to file a motion to suppress. Carroll 

further generally asserted his counsel was ineffective in failing to 

properly advise him as to the insufficiency of the State’s evidence to 

prove guilt as to the crimes charged, in failing to properly prepare him for 

the sentencing colloquy, and in failing to properly present a case in 

support of Carroll’s request for a deferred judgment. In its initial brief, 

the State asserted Carroll’s guilty plea waived any challenge to 

constitutional infirmities in the procedure prior to his guilty plea. 

Because Carroll’s initial brief did not expressly claim any errors resulting 
11

from counsel’s alleged ineffectiveness were intrinsic to the plea, the State 

contended Carroll failed on direct appeal to assert a valid challenge to 

the guilty plea. In his reply brief, Carroll expressly asserted for the first 

time that his guilty plea was rendered involuntary and unintelligent as a 

result of counsel’s ineffective assistance. 

We have repeatedly held we will not consider issues raised for the 

first time in a reply brief. Goodenow v. City Council, 574 N.W.2d 18, 27 

(Iowa 1998); Mueller v. St. Ansgar State Bank, 465 N.W.2d 659, 660 (Iowa 

1991); State v. Willet, 305 N.W.2d 454, 458 (Iowa 1981). Although the 

State correctly notes Carroll did not expressly assert in his initial brief 

that counsel’s ineffectiveness vitiated the knowing and voluntary 

character of the guilty plea, we conclude the assertion was properly 

addressed in his reply brief under the circumstances presented here. 

Carroll was not required to address the subject of waiver until the State 

raised it in its initial brief. Accordingly, we conclude the question of 

whether Carroll’s guilty plea was unknowing and involuntary as a 

consequence of his counsel’s ineffective assistance was properly raised 

for our review. Having concluded Carroll’s claim was properly raised, we 

next consider whether the record is sufficient in this case to determine 

whether counsel breached a duty, and whether any such breach caused 

prejudice. 

D. Sufficiency of the Record on Direct Appeal. Central to 

Carroll’s claims that his counsel provided ineffective assistance in 

connection with the guilty plea is the proposition that a motion should 

have been filed to suppress all evidence derived from the search of Wulf’s 

barn. As counsel has no duty to pursue a meritless issue, State v. 

Hoskins, 586 N.W.2d 707, 709 (Iowa 1998), the court must confront the 

question whether the search of Wulf’s barn violated Carroll’s Fourth 
12

Amendment rights. The “extent to which the Fourth Amendment 

protects people may depend upon where those people are.” Minnesota v. 

Carter, 525 U.S. 83, 88, 119 S. Ct. 469, 473, 142 L. Ed. 2d 373, 379

(1998). Carroll’s claim of Fourth Amendment protection depends upon 

the proposition that, as a social guest at a party, he had a reasonable 

expectation of privacy in Wulf’s barn. See Rakas v. Illinois, 439 U.S. 128, 

143–44, 99 S. Ct. 421, 430–31, 58 L. Ed. 2d 387, 400–02 (1978) (stating 

in order to claim the protection of the Fourth Amendment, a defendant 

must demonstrate that he personally has an expectation of privacy in the 

place searched, and that his expectation is reasonable). Although the 

text of the Fourth Amendment could be read as extending only to people 

in “their” houses, the Supreme Court has held that in some 

circumstances a person may have a legitimate expectation of privacy in 

the house of someone else. Carter, 525 U.S. at 89, 119 S. Ct. at 473, 

142 L. Ed. 2d at 379; see also State v. Ortiz, 618 N.W.2d 556, 561 (Iowa 

2000) (distinguishing a social guest from one who is permitted on the 

premises for the commercial purpose of engaging in commercial drug 

transactions). 

The determination of whether a person has a reasonable 

expectation of privacy with respect to a particular time and place “is 

made on a case-by-case basis, considering the unique facts of each 

particular situation.” State v. Breuer, 577 N.W.2d 41, 46 (Iowa 1998). 

The record in this case is inadequate in several particulars to determine 

whether Carroll can establish such an expectation during the gathering 

in Wulf’s barn. The relationship between Wulf and Carroll, and the 

frequency with which Carroll had previously, if ever, visited Wulf’s 

property is not disclosed. See Carter, 525 U.S. at 90, 119 S. Ct. at 473, 

142 L. Ed. 2d at 380 (discussing whether a social relationship existed 
13

between the defendant and the premises searched). We are also unable 

to discern from the record how long Carroll had been at the Wulf 

premises before the search occurred. See id. at 91, 119 S. Ct. at 474, 

142 L. Ed. 2d at 381 (noting the relatively short time defendants were 

present on the searched premises as a factor in deciding whether a 

reasonable expectation of privacy existed). The record also does not 

sufficiently disclose the nature of the place searched. Although the 

police report indicates a couch and bar were present on the top floor of 

the structure suggesting the presence of dwelling-like features, we believe 

the record is nonetheless inadequate to reveal the characteristics of the 

barn and its relationship, if any, to the Wulf dwelling. Furthermore, we 

believe a principled evaluation of the reasonableness of Carroll’s claimed 

expectation of privacy should be based on an understanding of the 

number of people invited to the party and the number of guests who were 

present at the time of the search. The record does not reveal whether the 

party was open to the public or limited to a circumscribed guest list.6

The record is also inadequate in at least one additional important 

respect. According to the police report, the investigating officers were 

unable by knocking on the exterior of the barn to rouse the attention of 

anyone inside. Soon thereafter the officers encountered a male and 

female exiting a garage on the Wulf premises.

 

7

 6The police report asserts the informant who reported the party to law 

enforcement officials claimed he had received five telephone calls from people inviting 

him to Wulf’s party.

 The report further asserts 

that when the officers inquired of the couple as to what was going on 

inside the barn, they did not directly respond, but instead invited the 

officers to “follow them to the party.” The record does not disclose the 

7The record is unclear whether the “garage” was part of the barn structure or 

connected to the Wulf residence that was located nearby on the same premises.
14

identity of the couple, nor does it offer evidence as to whether the couple 

had authority to invite the officers into the barn without a warrant.

III. Conclusion.

We affirm Carroll’s conviction. Because the record is inadequate to 

decide the claim of ineffective assistance of counsel, we preserve it for 

possible postconviction proceedings. 

DECISION OF THE COURT OF APPEALS VACATED; DISTRICT 

COURT JUDGMENT AFFIRMED.

All justices concur except Baker, J., who takes no part.